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Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones

[Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of t...

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Autores principales: He, Hua-Feng, Wang, Yuwan, Zou, Chun, Tu, Zheng, Xu, Yongquan, Yin, Junfeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8793066/
https://www.ncbi.nlm.nih.gov/pubmed/35097300
http://dx.doi.org/10.1021/acsomega.1c06177
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author He, Hua-Feng
Wang, Yuwan
Zou, Chun
Tu, Zheng
Xu, Yongquan
Yin, Junfeng
author_facet He, Hua-Feng
Wang, Yuwan
Zou, Chun
Tu, Zheng
Xu, Yongquan
Yin, Junfeng
author_sort He, Hua-Feng
collection PubMed
description [Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of the reaction. In this tandem reaction, Ag(2)O was employed as the media and Et(3)N was screened as the base to facilitate the reaction. A concise mechanism was proposed on the basis of the expansion of the substrates and theoretical analysis. Sonogashira type coupling coupled with intramolecular nucleophilic addition in one pot to construct the product, 3-ethylideneisobenzofuran-1(3H)-one.
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spelling pubmed-87930662022-01-28 Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones He, Hua-Feng Wang, Yuwan Zou, Chun Tu, Zheng Xu, Yongquan Yin, Junfeng ACS Omega [Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of the reaction. In this tandem reaction, Ag(2)O was employed as the media and Et(3)N was screened as the base to facilitate the reaction. A concise mechanism was proposed on the basis of the expansion of the substrates and theoretical analysis. Sonogashira type coupling coupled with intramolecular nucleophilic addition in one pot to construct the product, 3-ethylideneisobenzofuran-1(3H)-one. American Chemical Society 2022-01-11 /pmc/articles/PMC8793066/ /pubmed/35097300 http://dx.doi.org/10.1021/acsomega.1c06177 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle He, Hua-Feng
Wang, Yuwan
Zou, Chun
Tu, Zheng
Xu, Yongquan
Yin, Junfeng
Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title_full Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title_fullStr Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title_full_unstemmed Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title_short Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
title_sort ag(2)o-mediated tandem reaction between terminal alkyne and o-iodibenzoic acid: construction of 3-ethylideneisobenzofuran-1(3h)-ones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8793066/
https://www.ncbi.nlm.nih.gov/pubmed/35097300
http://dx.doi.org/10.1021/acsomega.1c06177
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